EP0864580A2 - Procédé de préparation de D-glucoronolactone - Google Patents

Procédé de préparation de D-glucoronolactone Download PDF

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Publication number
EP0864580A2
EP0864580A2 EP98104268A EP98104268A EP0864580A2 EP 0864580 A2 EP0864580 A2 EP 0864580A2 EP 98104268 A EP98104268 A EP 98104268A EP 98104268 A EP98104268 A EP 98104268A EP 0864580 A2 EP0864580 A2 EP 0864580A2
Authority
EP
European Patent Office
Prior art keywords
trehalose
glucuronolactone
oxidized
process according
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP98104268A
Other languages
German (de)
English (en)
Other versions
EP0864580A3 (fr
EP0864580B1 (fr
Inventor
Toshiki Tsuchioka
Tadashi Yamaguchi
Kunihiko Yuuen
Hiroto Chaen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chugoku Kayaku KK
Hayashibara Seibutsu Kagaku Kenkyujo KK
Original Assignee
Chugoku Kayaku KK
Hayashibara Biochemical Laboratories Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chugoku Kayaku KK, Hayashibara Biochemical Laboratories Co Ltd filed Critical Chugoku Kayaku KK
Publication of EP0864580A2 publication Critical patent/EP0864580A2/fr
Publication of EP0864580A3 publication Critical patent/EP0864580A3/fr
Application granted granted Critical
Publication of EP0864580B1 publication Critical patent/EP0864580B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04—Cyclic acetals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/04—Disaccharides

Definitions

  • This invention relates to a process for producing D-glucuronolactone, more specifically, to a process for producing D-glucuronolactone by oxidizing trehalose and then hydrolyzing the oxidized trehalose.
  • the present invention has been accomplished under these circumstances and aims at providing a process for producing D-glucuronolactone which gives high yield and which can be easily implemented on an industrial scale.
  • This object of the invention can be attained by a process for producing D-glucuronolactone comprising the steps of oxidizing trehalose, then hydrolyzing the oxidized trehalose to form D-glucuronolactone and recovering the same.
  • the sequence of reactions that take place in the process of the invention for producing D-glucuronolactone is indicated below by Scheme 1 (provided that the first reaction starts with ⁇ , ⁇ -trehalose):
  • the source and origin of the treahalose to be used in the invention are not limited in any particular way.
  • the applicable trehalose may be an extract from bacteria, fungi, algae or insects or it may be obatined from maltose by the action of a complex enzyme system consisting of maltose phosphorylase and trehalose phosphorylase; alaternatively, maltose may be directly converted to trehalose with a maltose-trehalose converting enzyme, or a partial hydrolyzate of starch may be saccharified enzymatically.
  • the trehalose produced by either the third or fourth method may be purified by a suitable method to produce trehalose of a higher purity and this is desirably used as the starting trehalose.
  • the trehalose content of the product is further enhanced by using the two enzymes in combination with a starch debranching enzyme such as isoamylase or pullulanase.
  • a starch debranching enzyme such as isoamylase or pullulanase.
  • the maltose-trehalose converting enzyme disclosed in Japanese Patent Public Disclosure Nos. 170977/1995, 263/1996, the specification of Japanese Patent Application No. 187901/1994 and Japanese Patent Public Disclosure No. 149980/1996 may be allowed to act on either maltose or a sugar composition containing maltose.
  • trehalose is dissolved in a suitable solvent, for example, at least one solvent selected from among water and straight-chain or branched lower alcohols such as methanol, ethanol, butanol and isopropyl alcohol and, thereafter, at least one known oxidizer selected from among inorganic nitrogen compounds such as nitric acid, nitrous acid and salts thereof, metal compounds such as manganese, chromium and lead compounds, halogens, inorganic halogen compounds, oxygen species such as air, oxygen and ozone, peroxides such as peroxonic acid, and organic compounds such as nitrobenzene, is added to oxidize the trehalose.
  • a suitable solvent for example, at least one solvent selected from among water and straight-chain or branched lower alcohols such as methanol, ethanol, butanol and isopropyl alcohol and, thereafter, at least one known oxidizer selected from among inorganic nitrogen compounds such as nitric acid, nitrous acid and salts thereof, metal compounds such as
  • Trehalose oxidation can advantageously be performed in the presence of an oxidizing catalyst such as platinum oxide, platinum on carbon, vanadium oxide or palladium on carbon, which are used to accelerate the oxidizing reaction, Trehalose can also be oxidized by electrooxidation or microbial oxidative fermentation.
  • an oxidizing catalyst such as platinum oxide, platinum on carbon, vanadium oxide or palladium on carbon, which are used to accelerate the oxidizing reaction
  • Trehalose can also be oxidized by electrooxidation or microbial oxidative fermentation.
  • water can advantageously be used as the solvent, oxygen, ozone or air as the oxidizer, and platinum oxide or platinum on carbon as the oxidizing catalyst.
  • the oxidation reaction temperature should be high enough to allow for the progress of the reaction but insufficient to decompose trehalose, oxidized trehalose and D-glucuronolactone; typically, the oxidation reaction temperature is selected from the range of ca. 0 - 200°C, preferably ca. about 20 - 150°C, more preferably ca. 40 - 130°C, most preferably ca. 60 - 100°C.
  • the time of oxidation reaction depends on the oxidizer used and the temperature and it is typically in the range of ca. 1 - 150 h, preferably ca. 5 - 80 h, more preferably ca. 10 - 30 h.
  • the oxidation reaction is preferably performed with pH adjustment, which is effectively done with pH typically in the range of 5 - 10, preferably 6 - 9, more preferably 7 - 8.
  • Any bases that will not Interfere with the reaction may be used for pH adjustment.
  • Examples that may be used include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogendcarbonate, potassium hydrogencarbonate, magnesium hydroxide, ferrous hydroxide, ammonia, and alkylamines (e.g. trimethylamine, triehylamine, dimethylamine, diethylamine, monomethylamine, monoethylamine and so forth),
  • oxidized trehalose can be produced in high yields of at least 95% relative to the trehalose used as the raw material.
  • Hydrolysis of the oxidized trehalose can be easily accomplished by reacting it with one or more hydrolyzers selected from among acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and tosic acid in one or more solvents selected from among water and straight-chain or branched lower alcohols such as methanol, ethanol, butanol and ispropyl alcohol.
  • hydrolyzers selected from among acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and tosic acid in one or more solvents selected from among water and straight-chain or branched lower alcohols such as methanol, ethanol, butanol and ispropyl alcohol.
  • Other methods of hydrolysis include the use of hydrolases.
  • the temperature during hydrolysis which depends on the hydrolase used is selected from the range of ca. 0 - 200°C, preferably ca. 20 - 150°C, more preferably ca. 40 - 130°C, most preferably ca. 60 - 100
  • reaction product which contains D-glucuronolatone can typically be used as such after the unreacted reagents and/or the solvents are separated by filtration, extraction, solid-liquid separation, fractional precipitation, dialysis distillation, and so forth.
  • Example 1-1 Preparation of oxidized trehalose
  • Example 1-2 Production of D-glucuronolactone from oxidized trehalose
  • Example 2-2 Production of D-glucuronolactone from oxidized trehalose
  • Example 3-2 Production of D-glucuronolactone from oxidized trehalose
  • Example 4-2 Production of D-glucuronolactone from oxidized trehalose
  • the present invention not only improves the yield off D-glucuronolactone; it also eliminates foaming from the process of production of D-glucuronolactone and, hence the throughput of D-glucuronolactone per batch is remarkably increased to achieve a significatn improvement in reactor's efficiency. Therefore, one may well say that the process of the invention for producing D-glucuronolactone is an industrially superior approach that features a by far higher efficiency in the production of D-glucuronolactone than the currently practiced processes.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP98104268A 1997-03-10 1998-03-10 Procédé de préparation de D-glucuronolactone Expired - Lifetime EP0864580B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP05507597A JP4153057B2 (ja) 1997-03-10 1997-03-10 Ｄ−グルクロノラクトンの製造方法
JP55075/97 1997-03-10
JP5507597 1997-03-10

Publications (3)

Publication Number Publication Date
EP0864580A2 true EP0864580A2 (fr) 1998-09-16
EP0864580A3 EP0864580A3 (fr) 1998-11-04
EP0864580B1 EP0864580B1 (fr) 2003-06-04

Family

ID=12988591

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98104268A Expired - Lifetime EP0864580B1 (fr) 1997-03-10 1998-03-10 Procédé de préparation de D-glucuronolactone

Country Status (6)

Country Link
US (1) US5912361A (fr)
EP (1) EP0864580B1 (fr)
JP (1) JP4153057B2 (fr)
KR (1) KR100538682B1 (fr)
DE (1) DE69815179T2 (fr)
TW (1) TW476759B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005002611A1 (fr) * 2003-06-27 2005-01-13 Indena S.P.A. Preparations destinees au traitement de troubles arthritiques
EP2049199B1 (fr) * 2006-08-08 2018-06-13 INDENA S.p.A. Compositions pour le traitement des maladies inflammatoires dégénératives chroniques

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6335464B1 (en) 1997-09-08 2002-01-01 Chugai Seiyaku Kabushiki Kaisha Process for selectively oxidizing primary hydroxyl groups of organic compounds, and resin containing adsorbed catalyst for use therein
JP2002153294A (ja) * 2000-11-21 2002-05-28 Hayashibara Biochem Lab Inc グルクロン酸類及び／又はｄ−グルクロノラクトンの製造方法とその用途
WO2005059152A1 (fr) * 2003-12-18 2005-06-30 Cerestar Holding B.V. Oxydation de carbohydrates au moyen de peroxydases et de radicaux nitroxy
US7923231B2 (en) * 2004-12-17 2011-04-12 Cargill, Incorporated Production of glucuronic acid using myo-inositol oxygenase from cryptococcus neoformans
JP2006314223A (ja) * 2005-05-11 2006-11-24 Yokohama Kokusai Bio Kenkyusho:Kk グルクロン酸及び／又はグルクロノラクトンの製造方法
US8530186B2 (en) 2007-05-08 2013-09-10 Ensuiko Sugar Refining Co., Ltd. Method for producing glucuronic acid by glucuronic acid fermentation
JP6046338B2 (ja) 2011-10-27 2016-12-14 株式会社Ihi ラジカル抑制剤
KR20230119689A (ko) * 2020-12-14 2023-08-16 솔루젠, 인코포레이티드 고순도 히드록시카르복시산 조성물 및 그 제조방법

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB670929A (en) * 1949-12-17 1952-04-30 Corn Prod Refining Co Improvements in or relating to a method of preparing uronic acids and derivaties thereof
GB727471A (en) * 1950-10-17 1955-04-06 Corn Prod Refining Co Improvements in or relating to a process of recovering glucuronolactone
ATE182359T1 (de) * 1992-12-28 1999-08-15 Hayashibara Biochem Lab Nichtreduzierendes saccharidbildendes enzym, und dessen herstellung und verwendungen
JP3559585B2 (ja) * 1993-06-03 2004-09-02 株式会社林原生物化学研究所 トレハロース遊離酵素とその製造方法並びに用途
JP3633648B2 (ja) * 1993-07-20 2005-03-30 株式会社林原生物化学研究所 マルトース・トレハロース変換酵素とその製造方法並びに用途
US5871993A (en) * 1994-02-23 1999-02-16 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo DNA encoding enzyme, recombinant DNA and enzyme, transformant, and their preparations and uses
KR100374449B1 (ko) * 1994-03-07 2003-09-06 가부시끼가이샤 하야시바라 세이부쓰 가가꾸 겐꾸조 효소를인코우드하는디엔에이(dna),재조합디엔에이(dna)와효소,형질전환체및이들의제조방법과용도
JP3650632B2 (ja) * 1994-06-16 2005-05-25 株式会社林原生物化学研究所 マルトースをトレハロースに変換する組換え型酵素
US5714368A (en) * 1994-06-24 1998-02-03 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Thermostable non-reducing saccharide-forming enzyme its production and uses
JP3810457B2 (ja) * 1994-10-01 2006-08-16 株式会社林原生物化学研究所 マルトースをトレハロースに変換する組換え型耐熱性酵素
KR100670929B1 (ko) * 2005-06-29 2007-01-17 서울옵토디바이스주식회사 플립칩 구조의 발광 소자 및 이의 제조 방법
KR100727471B1 (ko) * 2005-12-01 2007-06-13 세메스 주식회사 유체 공급 장치 및 방법

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005002611A1 (fr) * 2003-06-27 2005-01-13 Indena S.P.A. Preparations destinees au traitement de troubles arthritiques
JP2007513051A (ja) * 2003-06-27 2007-05-24 インデナ エッセ ピ ア 関節炎の状態を治療するための製剤
AU2004253242B2 (en) * 2003-06-27 2010-02-18 Indena S.P.A. Formulations for the treatment of arhritis conditions
US8343554B2 (en) 2003-06-27 2013-01-01 Indena S.P.A. Formulations for the treatment of arthritis conditions
EP2049199B1 (fr) * 2006-08-08 2018-06-13 INDENA S.p.A. Compositions pour le traitement des maladies inflammatoires dégénératives chroniques
NO343552B1 (no) * 2006-08-08 2019-04-01 Indena Spa Sammensetninger for behandling av kroniske degenerative inflammatoriske tilstander

Also Published As

Publication number Publication date
DE69815179D1 (de) 2003-07-10
JPH10251263A (ja) 1998-09-22
KR100538682B1 (ko) 2006-02-28
EP0864580A3 (fr) 1998-11-04
DE69815179T2 (de) 2004-05-19
TW476759B (en) 2002-02-21
JP4153057B2 (ja) 2008-09-17
KR19980080086A (ko) 1998-11-25
EP0864580B1 (fr) 2003-06-04
US5912361A (en) 1999-06-15

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